Cheap Flights from Milan to Chicago, IL from $342

Return flight: Chicago – Milan

On Cheapflightsplus.com you will find 705 connecting flights from Milan to Chicago. You can compare airfare deals from 37 airlines and multiple travel sites from $342, book and save on cheap plane tickets and last minute offers. Also check out MIL-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Milan to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $342 (one-way), $586 (round-trip).
Direct flights
  • Check to choose departure date Check to choose departure date
Check prices for return flight
Find flights
Full flight schedule will help you in detecting at what time planes fly from Milan to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
06:20 — 15:30
06:20 — 08:15 TP829 TAP Portugal
Milan — Lisbon
3h 45m stop
11:55 — 15:30 TP243 TAP Portugal
Lisbon — Chicago
16h 10m
including layover
Find flight
from$474
06:25 — 15:15
06:25 — 07:45 UA9305 United Airlines
Milan — Frankfurt
5h 5m stop
12:50 — 15:15 UA906 United Airlines
Frankfurt — Chicago
15h 50m
including layover
Find flight
from$759
07:00 — 10:10
+1 day
07:00 — 12:00 TK1878 Turkish Airlines
Milan — Istanbul
19h 35m stop
07:35 — 10:10 TK185 Turkish Airlines
Istanbul — Chicago
34h 10m
including layover
Find flight
from$517
07:15 — 17:20
07:15 — 10:50 U23969 EasyJet
Milan — Reykjavik
5h 55m stop
16:45 — 17:20 FI853 Icelandair
Reykjavik — Chicago
17h 5m
including layover
Find flight
from$574
09:30 — 10:50
+1 day
09:30 — 11:10 JU417 Air Serbia
Milan — Belgrade
19h 50m stop
07:00 — 10:50 JU506 Air Serbia
Belgrade — Chicago
32h 20m
including layover
Find flight
from$531
09:40 — 15:50
09:40 — 11:40 D83751 Djibouti Airlines
Milan — Copenhagen
1h 55m stop
13:35 — 15:50 SK943 SAS
Copenhagen — Chicago
13h 10m
including layover
Find flight
from$584
10:30 — 14:30
+1 day
10:30 — 12:50 IB672 Iberia
Milan — Madrid
22h 45m stop
11:35 — 14:30 IB341 Iberia
Madrid — Chicago
35h
including layover
Find flight
from$583
10:50 — 14:30
+1 day
10:50 — 13:10 UX1066 Air Europa
Milan — Madrid
22h 25m stop
11:35 — 14:30 IB341 Iberia
Madrid — Chicago
34h 40m
including layover
Find flight
from$579
11:55 — 22:55
11:55 — 14:50 NO787 Neos
Milan — New York
6h 25m stop
21:15 — 22:55 NK225 Spirit Airlines
New York — Chicago
18h
including layover
Find flight
from$471
11:55 — 15:30
+1 day
11:55 — 13:50 TP823 TAP Portugal
Milan — Lisbon
22h 5m stop
11:55 — 15:30 TP243 TAP Portugal
Lisbon — Chicago
34h 35m
including layover
Find flight
from$486
12:15 — 18:45
12:15 — 13:25 BA587 British Airways
Milan — London
2h 20m stop
15:45 — 18:45 BA297 British Airways
London — Chicago
13h 30m
including layover
Find flight
from$909
13:15 — 18:45
13:10 — 14:20 BA577 British Airways
Milan — London
1h 20m stop
15:45 — 18:45 BA297 British Airways
London — Chicago
12h 30m
including layover
Find flight
from$908
13:30 — 17:20
+1 day
13:30 — 17:15 W46453 Aero Services Executive
Milan — Reykjavik
23h 30m stop
16:45 — 17:20 FI853 Icelandair
Reykjavik — Chicago
34h 50m
including layover
Find flight
from$504
14:40 — 18:25
+1 day
14:40 — 19:35 TK1896 Turkish Airlines
Milan — Istanbul
19h 55m stop
15:30 — 18:25 TK5 Turkish Airlines
Istanbul — Chicago
34h 45m
including layover
Find flight
from$636
14:40 — 10:10
+1 day
14:40 — 19:35 TK1896 Turkish Airlines
Milan — Istanbul
12h stop
07:35 — 10:10 TK185 Turkish Airlines
Istanbul — Chicago
26h 30m
including layover
Find flight
from$714
15:15 — 15:15
+1 day
15:15 — 21:30 RJ104 Royal Jordanian
Milan — Amman
13h 5m stop
10:35 — 15:15 RJ263 Royal Jordanian
Amman — Chicago
31h
including layover
Find flight
from$676
15:50 — 16:50
+1 day
15:30 — 16:40 BA591 British Airways
Milan — London
21h 10m stop
14:10 — 17:00 BA1542 British Airways
London — Chicago
32h
including layover
Find flight
from$917
16:50 — 16:50
+1 day
16:35 — 17:40 BA575 British Airways
Milan — London
20h 15m stop
14:10 — 17:00 BA1542 British Airways
London — Chicago
31h
including layover
Find flight
from$918
16:50 — 13:55
+1 day
16:35 — 17:40 BA575 British Airways
Milan — London
17h 5m stop
11:00 — 13:55 BA295 British Airways
London — Chicago
28h 5m
including layover
Find flight
from$920
17:45 — 15:30
+1 day
17:45 — 19:40 TP827 TAP Portugal
Milan — Lisbon
16h 15m stop
11:55 — 15:30 TP243 TAP Portugal
Lisbon — Chicago
28h 45m
including layover
Find flight
from$479
18:20 — 14:30
+1 day
18:20 — 20:40 UX1062 Air Europa
Milan — Madrid
14h 55m stop
11:35 — 14:30 IB341 Iberia
Madrid — Chicago
27h 10m
including layover
Find flight
from$580
18:35 — 10:10
+1 day
18:35 — 23:35 TK1876 Turkish Airlines
Milan — Istanbul
8h stop
07:35 — 10:10 TK185 Turkish Airlines
Istanbul — Chicago
22h 35m
including layover
Find flight
from$517
19:10 — 14:30
+1 day
19:10 — 21:30 IB676 Iberia
Milan — Madrid
14h 5m stop
11:35 — 14:30 IB341 Iberia
Madrid — Chicago
26h 20m
including layover
Find flight
from$585
19:55 — 10:50
+1 day
19:55 — 21:35 JU419 Air Serbia
Milan — Belgrade
9h 25m stop
07:00 — 10:50 JU506 Air Serbia
Belgrade — Chicago
21h 55m
including layover
Find flight
from$513
20:15 — 15:50
+1 day
20:15 — 22:25 U23925 EasyJet
Milan — Copenhagen
14h 55m stop
13:35 — 15:50 SK943 SAS
Copenhagen — Chicago
26h 35m
including layover
Find flight
from$604
20:25 — 14:30
+1 day
20:25 — 22:50 IB666 Iberia
Milan — Madrid
12h 45m stop
11:35 — 14:30 IB341 Iberia
Madrid — Chicago
25h 5m
including layover
Find flight
from$586
21:25 — 13:55
+1 day
20:45 — 21:55 BA581 British Airways
Milan — London
12h 25m stop
11:00 — 13:55 BA295 British Airways
London — Chicago
23h 30m
including layover
Find flight
from$909
*Departure and arrival times - local. Updated on December 26, 2024

Flight Information

Below we will explain in detail what the flights cost on the destination from Milan to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Milan and Chicago is 7289 miles. Time difference between the cities is 7h. Airplanes depart 03:15 to 23:40 from 4 Milan airports and arrive 03:15 to 23:40 to 7 Chicago airports. Average flight time is 27h 55m.

  • The fastest flight 11h 45m
  • Average flight time 27h 55m
  • The earliest flight 03:15
  • The latest flight 23:40
  • Distance 4530 ml

The cheapest months to travel to Chicago are february (from 342 $), january (from 359 $), december (from 414 $).

The most expensive months are november (from 436 $), december (from 414 $), january (from 359 $).

What is the lowest airfare Milan to Chicago?

The cheapest plane ticket found by our users is $342. This airfare is for economy class on one-way U23969 flight by EasyJet for February 21, 2025 which leaves Malpensa in Milan at 07:15 am and arrives at Chicago Midway at 20:08.

Economy class
$342
Find
Business class
?
Find
First class
?
Find

Popular Airlines on the Route

The flight Milan — Chicago is served by 37 regular airlines and 6 low-cost airlines. Most of the flights on this route are operated by United Airlines - 8 departures per week at the price of from $ 759 . And the most expensive tickets are offered by British Airways airline - from $ 2980.

Direct flights

There’re no direct flights on this route. Try flights with stops.

Connecting Flights

There are 705 flights with layovers on the route. The fastest connecting flight is UA9305 by United Airlines takes 11h 45m and the cheapest is U23969 by EasyJet for $342.

See more connecting flights

Airports

You can fly from Milan to Chicago from 4 airports (Linate, Malpensa, Milan Bergamo (Orio al Serio), Segrate).

Milan airports

  • Linate-LIN
    from $372
    Find
  • Malpensa-MXP
    from $342
    Find
  • Milan Bergamo (Orio al Serio)-BGY
    from $468
    Find
  • Segrate-SWK
    Find

Chicago airports

  • O'Hare International-ORD
    Find
  • Midway-MDW
    Find
  • Dupage County-DPA
    Find
  • Chicago FSS-CHI
    Find
  • Merrill C Meigs (closed)-CGX
    Find
  • Pal-Waukee-PWK
    Find
  • Chicago NAS-NOH
    Find

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

Back